Sodium Hydroxide → HCID 15082755, compound

HRID 439840Notes

Reaction equation

HRID 439840 reaction equation
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[C:3]1[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C:4]=1[NH:5]2.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[C@H:3]1[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][C@H:4]1[NH:5]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 131294105,6-Dihydroindeno[2,1-b]indole

Product 1

HCID 15082755HCID 15082755, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,6-Dihydroindeno[2,1-b]indole (185 mg, 0.9 mmol) was reacted with sodium cyanoborohydride (310 mg, 5 mmol), in glacial acetic acid (5 cm3), for six hours. The solution was poured into ice/water, and stirred for one hour. It was then neutralised with sodium hydroxide, and the white solid which formed was collected by filtration, washed with water, dried and purified by "flash" chromatography (10% EtOAc/petrol 60°-80° C., Rf 30% EtOAc/petrol (60°-80° C.) 0.6) to yield the title compound as a colourless solid. Yield: (81 mg, (43%) M.p. 85°-86° C. 1H NMR (CDCl3) δ: 3.09 (1H, dd,), 3.33 (1H, dd,), 3.45 (1H, br,), 4.74 (1H, d,), 4.82 (1H, ddd,), 6.55 (1H, d,), 6.73 (1H, ddd,), 7.00 (1H, ddd,), 7.1- 7.4 (4H, m).

Workup

  1. customthe white solid which formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried
  5. custompurified by "flash" chromatography (10% EtOAc/petrol 60°-80° C., Rf 30% EtOAc/petrol (60°-80° C.) 0.6)

Sources & evidence

ORD record
ord-869055502ed74eec8f1bb2fdcb6ccc1b
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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